1-Propanol, 3-amino-2,2-dimethyl- → 5-Chloro-1-(5-tert-butyl-2-methoxybenzyl)-1H-indole-2-carboxylic acid (3-hydroxy-2,2-dimethylpropyl)amide

HRID 2242354

Reaktionsgleichung

Reaktionsgleichung von HRID 2242354
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[C:24]([C:28]1[CH:29]=[CH:30][C:31]([O:48][CH3:49])=[C:32]([CH:47]=1)[CH2:33][N:34]1[C:42]2[C:37](=[CH:38][C:39]([Cl:43])=[CH:40][CH:41]=2)[CH:36]=[C:35]1[C:44](O)=[O:45])([CH3:27])([CH3:26])[CH3:25].[NH2:50][CH2:51][C:52]([CH3:56])([CH3:55])[CH2:53][OH:54]>C(Cl)Cl.O>[OH:54][CH2:53][C:52]([CH3:56])([CH3:55])[CH2:51][NH:50][C:44]([C:35]1[N:34]([CH2:33][C:32]2[CH:47]=[C:28]([C:24]([CH3:27])([CH3:25])[CH3:26])[CH:29]=[CH:30][C:31]=2[O:48][CH3:49])[C:42]2[C:37]([CH:36]=1)=[CH:38][C:39]([Cl:43])=[CH:40][CH:41]=2)=[O:45]

Komponenten

7

Edukt 4

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 685507621-(5-tert-butyl-2-methoxybenzyl)-5-chloro-1H-indole-2-carboxylic acid

Produkt 1

HCID 592053975-Chloro-1-(5-tert-butyl-2-methoxybenzyl)-1H-indole-2-carboxylic acid (3-hydroxy-2,2-dimethylpropyl)amideAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g, 0.57 mmol) followed by 1-hydroxybenzotriazole hydrate (0.08 g, 0.59 mmol) were added to a solution of 1-(5-tert-butyl-2-methoxybenzyl)-5-chloro-1H-indole-2-carboxylic acid (0.20 g, 0.54 mmol) in DCM (10.0 ml) and after stirring for 10 min, 3-amino-2,2-dimethylpropan-1-ol (67 mg, 0.65 mmol) was added. After stirring for 17.5 h, water (10 ml) was added, the layers separated, the organic washed with water (3×15 ml) and dried with magnesium sulfate. Purification was achieved by chromatography on silica using DCM:methanol (3:1) as eluent. Crystallisation of the crude afforded the title compound as a white solid (90 mg, 36%).

Aufarbeitung

  1. stirringAfter stirring for 17.5 h
  2. customthe layers separated
  3. washthe organic washed with water (3×15 ml)
  4. dry with materialdried with magnesium sulfate
  5. customPurification
  6. customCrystallisation of the crude

Quellen und Nachweise

ORD-Eintrag
ord-806f0533ae81420fb5109f67b97a3d9a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671080B2

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